Sodium cyanoborohydride → 5-[4-[2-[(3-chloro-beta-hydroxyphenethyl)amino]propyl]phenyl]-3,4-dihydro-6-methyl-2(1H)-pyridinone

HRID 465431Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 465431
C(=O)(O)O.[OH:5][CH:6]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([Cl:15])[CH:10]=1)[CH2:7][NH2:8].[CH2:16]([C:20]1[CH:25]=[CH:24][C:23]([C:26]2[CH2:27][CH2:28][C:29](=[O:33])[NH:30][C:31]=2[CH3:32])=[CH:22][CH:21]=1)[C:17]([CH3:19])=O.C([BH3-])#N.[Na+]>CO>[Cl:15][C:11]1[CH:10]=[C:9]([CH:14]=[CH:13][CH:12]=1)[CH:6]([OH:5])[CH2:7][NH:8][CH:17]([CH3:19])[CH2:16][C:20]1[CH:21]=[CH:22][C:23]([C:26]2[CH2:27][CH2:28][C:29](=[O:33])[NH:30][C:31]=2[CH3:32])=[CH:24][CH:25]=1

Komponenten

5

Edukt 3

HCID 5003444Sodium cyanoborohydrideHCID 198745593,4-dihydro-5-(4-acetonylphenyl)-6-methyl-2(1H)-pyridoneHCID 678659382-(3-Chlorophenyl)-2-hydroxyethylamine carbonate

Produkt 1

HCID 198745455-[4-[2-[(3-chloro-beta-hydroxyphenethyl)amino]propyl]phenyl]-3,4-dihydro-6-methyl-2(1H)-pyridinone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A mixture of 2-hydroxy-2-(3-chlorophenyl)ethanamine carbonate (0.34 g) and 3,4-dihydro-5-(4-acetonylphenyl)-6-methyl-2(1H)-pyridone (0.4 g) was dissolved in methanol (30 ml). Sodium cyanoborohydride (0.1 g) was added and the mixture was allowed to stand at room tempeature for 16 hr. The solvent was evaporated, the residue partitioned between ethylacetate and water, the organic layer separated, dried (MgSO4) and evaporated to give an oil which was chromatographed on Silica. Elution with methanol-chloroform (3:97) gave 5-[4-[2-[(3-chloro-β-hydroxyphenethyl)amino]propyl]phenyl]-3,4-dihydro-6-methyl-2(1H)-pyridinone as a 1:1 mixture of diastereoismers, m.pt. 103°-106° C. (ethyl acetate ether).

Aufarbeitung

  1. customThe solvent was evaporated
  2. customthe residue partitioned between ethylacetate and water
  3. customthe organic layer separated
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customto give an oil which
  7. customwas chromatographed on Silica
  8. washElution with methanol-chloroform (3:97)

Quellen und Nachweise

ORD-Eintrag
ord-1c9ff312ad244c44b1b8aa0889cce51c
Quelldatensatz
uspto-grants-1992_10
Patentnummer
US05153210

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